Molecular and crystal structure of 5-phenyl, 5-m-nitrophenyl, and 5-spirocyclopentane derivatives of 3-amino-2,4,4-tricyanobicyclo [4,4,0] deca-2,10-diene

Abstract

To examine the ability of 3-amino-2,4,4-tricyanobicyclo[4,4,0]deca-2,10-dienes (I) to form dimeric associates, we have investigated molecular and crystal structure of three derivatives of (I): 5-phenyl (II), 5-m-nitrophenyl (III), and 5-spirocyclopentano (IV). Hydrogen bonding via the aminonitrile fragment leads to formation of centrosymmetric dimeric associates in compounds (II, III) and a chain structure in (IV). Crystal data for (II): space group P2₁/c, a=8.726(3), b=15.879(5), c=15.597(5) Å, α=γ=90, β=105.13(2)⁰, V=2086.2 ų, Z=4, R=0.093; for (III): space group C2/c, a=24.725(8), b=9.004(5), c=24.391(8) Å, α=γ=90, β=125.36(2)⁰, V=4428.2ų, Z=8, R=0.080; for (IV): space group C2/c, a=24.443(8), b=10.240(5), c=16.645(6) Å, α=γ=90, β=108.89(2)⁰, V=3941.8 ų, Z=8, R=0.089.